Organic molecules for use in optoelectronic devices

ABSTRACT

Organic molecules are provided for use in organic optoelectronic devices. The organic molecules are purely organic molecules, i.e., they do not contain any metal ions. The organic molecules exhibit emission maxima in the blue, sky-blue or green spectral range. The organic molecules exhibit emission maxima between 420 nm and 520 nm, between 440 nm and 495 nm, or between 450 nm and 470 nm. The photoluminescence quantum yields of the organic molecules are 20% or more. The molecules exhibit thermally activated delayed fluorescence (TADF). Use of the molecules in an optoelectronic device, e.g., an organic light-emitting diode (OLED) leads to higher efficiencies of the device. Corresponding OLEDs have higher stabilities than OLEDs with known emitter materials and comparable color.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to German Patent Application No. DE 102017 122 471.8, filed Sep. 27, 2017, the disclosure of which isincorporated by reference herein in its entirety.

FIELD OF INVENTION

The invention relates to organic molecules and their use in organiclight-emitting diodes (OLEDs) and in other optoelectronic devices.

SUMMARY

The invention relates to organic compounds for the use in optoelectronicdevices. According to the invention, the organic compound has

-   -   a first chemical moiety with a structure of formula I,

and

-   -   two second chemical moieties, each independently from another        with a structure of formula II,

wherein the first chemical moiety is linked to each of the two secondchemical moieties via a single bond;

wherein

-   T, V, W, X and Y are selected from the group consisting of the    binding site of a single bond linking the first chemical moiety to    one of the two second chemical moieties, R^(A) and R¹;-   R^(T), R^(V), R^(W), R^(X) and R^(Y) are selected from the group    consisting of the binding site of a single bond linking the first    chemical moiety to one of the two second chemical moieties, CN and    R².

BRIEF DESCRIPTION OF THE DRAWINGS

Exemplary embodiments of the present invention will be described belowin more detail, with reference to the accompanying drawings, of which:

FIG. 1 is an emission spectrum of example 1 (10% by weight) in PMMA.

FIG. 2 is an emission spectrum of example 2 (10% by weight) in PMMA.

FIG. 3 is an emission spectrum of example 3 (10% by weight) in PMMA.

DETAILED DESCRIPTION OF EXEMPLARY EMBODIMENTS OF THE INVENTION

Exemplary embodiments of the invention will now be discussed in furtherdetail. This invention may, however, be embodied in many different formsand should not be construed as limited to the embodiments set forthherein.

The object of the present invention is to provide molecules which aresuitable for use in organic optoelectronic devices.

This object is achieved by the invention which provides a new class oforganic molecules.

According to the invention the organic molecules are purely organicmolecules, i.e. they do not contain any metal ions in contrast to metalcomplexes known for use in organic optoelectronic devices.

According to the present invention, the organic molecules exhibitemission maxima in the blue, sky-blue or green spectral range. Theorganic molecules exhibit in particular emission maxima between 420 nmand 520 nm, preferably between 440 nm and 495 nm, more preferablybetween 450 nm and 470 nm. The photoluminescence quantum yields of theorganic molecules according to the invention are, in particular, 20% ormore. The molecules according to the invention exhibit in particularthermally activated delayed fluorescence (TADF). The use of themolecules according to the invention in an optoelectronic device, forexample an organic light-emitting diode (OLED), leads to higherefficiencies of the device.

Corresponding OLEDs have a higher stability than OLEDs with knownemitter materials and comparable color.

The organic light-emitting molecules of the invention comprise orconsist of a first chemical moiety comprising or consisting of astructure of formula I,

and

-   -   two second chemical moieties, each independently from another        comprising or consisting of a structure of formula II,

wherein the first chemical moiety is linked to each of the two secondchemical moieties via a single bond.

T, V, W, X and Y are each selected from the group consisting of thebinding site of a single bond linking the first chemical moiety to oneof the two second chemical moieties, R^(A) (bonded via the single bondmarked with $ in Formula A1) and R¹.

R^(A) is consisting of a structure of formula A1,

wherein $ represents the binding site of the single bond connectingR^(A) and the first chemical moiety.

-   A^(I), A^(II), A^(III), A^(IV) and A^(V) are each selected from the    group consisting of CF₃ and R^(I).-   R^(T), R^(V), R^(W), R^(X) and R^(Y) are each selected from the    group consisting of the binding site of a single bond linking the    first chemical moiety to one of the two second chemical moieties, CN    and R².

# represents the binding site of a single bond linking the secondchemical moieties to the first chemical moiety;

Z is at each occurrence independently from another selected from thegroup consisting of a direct bond, CR³R⁴, C═CR³R⁴, C═O, C═NR³, NR³, O,SiR³R⁴, S, S(O) and S(O)₂;

R¹ is at each occurrence independently from another selected from thegroup consisting of

hydrogen,

deuterium,

C₁-C₅-alkyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;

C₂-C₈-alkenyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;

C₂-C₈-alkynyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium; and

C₆-C₁₈-aryl,

-   -   which is optionally substituted with one or more substituents        selected from the group consisting of hydrogen, deuterium, OPh,        C₁-C₅-alkyl, C₂-C₅-alkenyl and C₂-C₅-alkynyl.

R² is at each occurrence independently from another selected from thegroup consisting of

hydrogen,

deuterium,

C₁-C₅-alkyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;

C₂-C₈-alkenyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;

C₂-C₈-alkynyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium; and

C₆-C₁₈-aryl,

-   -   which is optionally substituted with one or more substituents        selected from the group consisting of hydrogen, deuterium, OPh,        C₁-C₅-alkyl, C₂-C₅-alkenyl and C₂-C₅-alkynyl.

R^(I) is at each occurrence independently from another selected from thegroup consisting of

hydrogen,

deuterium,

C₁-C₅-alkyl,

-   -   wherein one or more hydrogen atoms are optionally substituted by        deuterium; and

C₆-C₁₈-aryl,

-   -   which is optionally substituted with one or more substituents        R⁶.

R^(a), R³ and R⁴ is at each occurrence independently from anotherselected from the group consisting of hydrogen, deuterium, N(R⁵)₂, OR⁵,Si(R⁵)₃, B(OR⁵)₂, OSO₂R⁵, CF₃, CN, F, Br, I,

C₁-C₄₀-alkyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₁-C₄₀-alkoxy,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₁-C₄₀-thioalkoxy,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₂-C₄₀-alkenyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₂-C₄₀-alkynyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₆-C₆₀-aryl,

-   -   which is optionally substituted with one or more substituents        R⁵; and

C₃-C₅₇-heteroaryl,

-   -   which is optionally substituted with one or more substituents        R⁵.

R⁵ is at each occurrence independently from another selected from thegroup consisting of hydrogen, deuterium, N(R⁶)₂, OR⁶, Si(R⁶)₃, B(OR⁶)₂,OSO₂R⁶, CF₃, CN, F, Br, I,

C₁-C₄₀-alkyl,

-   -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;

C₁-C₄₀-alkoxy,

-   -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;

C₁-C₄₀-thioalkoxy,

-   -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;

C₂-C₄₀-alkenyl,

-   -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;

C₂-C₄₀-alkynyl,

-   -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;

C₆-C₆₀-aryl,

-   -   which is optionally substituted with one or more substituents        R⁶; and

C₃-C₅₇-heteroaryl,

-   -   which is optionally substituted with one or more substituents        R⁶.

R⁶ is at each occurrence independently from another selected from thegroup consisting of hydrogen, deuterium, OPh, CF₃, CN, F,

C₁-C₅-alkyl,

-   -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;

C₁-C₅-alkoxy,

-   -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;

C₁-C₅-thioalkoxy,

-   -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;

C₂-C₅-alkenyl,

-   -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;

C₂-C₅-alkynyl,

-   -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;

C₆-C₁₈-aryl,

-   -   which is optionally substituted with one or more C₁-C₅-alkyl        substituents;

C₃-C₁₇-heteroaryl,

-   -   which is optionally substituted with one or more C₁-C₅-alkyl        substituents;

N(C₆-C₁₈-aryl)₂,

N(C₃-C₁₇-heteroaryl)₂; and

N(C₃-C₁₇-heteroaryl)(C₆-C₁₈-aryl).

Optionally, the substituents R^(a), R³, R⁴ or R⁵, independently fromeach other, form a mono- or polycyclic, aliphatic, aromatic and/orbenzo-fused ring system with one or more substituents R^(a), R³, R⁴, orR⁵.

According to the invention, exactly one (one and only one) substituentselected from the group consisting of T, V, W, X and Y is R^(A); exactlyone substituent selected from the group consisting of R^(T), R^(V),R^(W), R^(X) and R^(Y) is CN; exactly one substituent selected from thegroup consisting of T, V, W, X and Y represents the binding site of asingle bond linking the first chemical moiety and one of the two secondchemical moieties and exactly one substituent selected from the groupconsisting of R^(T), R^(V), R^(W), R^(X) and R^(Y) represents thebinding site of a single bond linking the first chemical moiety and oneof the two second chemical moieties; exactly two substituents selectedfrom the group consisting of A^(I), A^(II), A^(III), A^(IV) and A^(V)are CF₃.

In one embodiment of the organic molecule of the invention, exactly onesubstituent selected from the group consisting of T, V and W is R^(A);exactly one substituent selected from the group consisting of R^(T),R^(V) and R^(W) is CN; exactly one substituent selected from the groupconsisting of W, Y and X represents the binding site of a single bondlinking the first chemical moiety and one of the two second chemicalmoieties and exactly one substituent selected from the group consistingof R^(W), R^(X) and R^(Y) represents the binding site of a single bondlinking the first chemical moiety and one of the two second chemicalmoieties; and apart from that the aforementioned definitions apply.

In one embodiment of the invention, T is selected from the groupconsisting of R^(A) and R¹;

-   V is selected from the group consisting of R^(A) and R¹;-   W is selected from the group consisting of the binding site of a    single bond linking the first chemical moiety to one of the two    second chemical moieties, R^(A) and R¹;-   X is selected from the group consisting of the binding site of a    single bond linking the first chemical moiety to one of the two    second chemical moieties and R¹;-   Y is selected from the group consisting of the binding site of a    single bond linking the first chemical moiety to one of the two    second chemical moieties and R¹;-   R^(V) is selected from the group consisting of CN and R²;-   R^(T) is selected from the group consisting of CN and R²;-   R^(W) is selected from the group consisting of the binding site of a    single bond linking the first chemical moiety to one of the two    second chemical moieties, CN and R²;-   R^(X) is selected from the group consisting of the binding site of a    single bond linking the first chemical moiety to one of the two    second chemical moieties and R²;-   R^(Y) is selected from the group consisting of the binding site of a    single bond linking the first chemical moiety to one of the two    second chemical moieties and R²;

wherein:

exactly one substituent selected from the group consisting of T, V and Wis R^(A); exactly one substituent selected from the group consisting ofR^(T), R^(V) and R^(W) is CN; exactly one substituent selected from thegroup consisting of W, Y and X represents the binding site of a singlebond linking the first chemical moiety and one of the two secondchemical moieties; exactly one substituent selected from the groupconsisting of R^(W), R^(X) and R^(Y) represents the binding site of asingle bond linking the first chemical moiety and one of the two secondchemical moieties;

and apart from that the aforementioned definitions apply.

In one embodiment of the invention, the first chemical moiety comprisesor consists of a structure of Formula Ia-1:

wherein

Y^(D) represents the binding site of a single bond linking the firstchemical moiety and one of the two second chemical moieties,

R^(YD) represents the binding site of a single bond linking the firstchemical moiety and one of the two second chemical moieties,

Q is independently from each other at each occurrence selected from thegroup consisting of R¹ and R^(A),

R^(Q) is independently from each other at each occurrence selected fromthe group consisting of R² and CN,

wherein exactly one substituent selected from the group consisting ofR^(Q) is CN,

wherein exactly one substituent selected from the group consisting of Qis R^(A),

and apart from that the aforementioned definitions apply.

In one embodiment, R¹ and R² is at each occurrence independently fromanother selected from the group consisting of hydrogen (H), methyl,mesityl, tolyl and phenyl. The term tolyl comprises 2-tolyl, 3-tolyl and4-tolyl.

In one embodiment, R¹, R², and R^(I) is at each occurrence independentlyfrom another selected from the group consisting of hydrogen (H), methyl,and phenyl.

In one embodiment, R^(T) is CN.

In one embodiment, R^(V) is CN.

In one embodiment, R^(W) is CN.

In one embodiment, R^(X) is CN.

In one embodiment, R^(Y) is CN.

In one embodiment, T is R^(A).

In one embodiment, V is R^(A).

In one embodiment, W is R^(A).

In one embodiment, X is R^(A).

In one embodiment, Y is R^(A).

In one embodiment, R^(T) is CN and Y is R^(A).

In one embodiment, R^(T) is CN and X is R^(A).

In one embodiment, R^(T) is CN and W is R^(A).

In one embodiment, R^(T) is CN and V is R^(A).

In one embodiment, R^(T) is CN and T is R^(A).

In one embodiment, R^(V) is CN and Y is R^(A).

In one embodiment, R^(V) is CN and X is R^(A).

In one embodiment, R^(V) is CN and W is R^(A).

In one embodiment, R^(V) is CN and V is R^(A).

In one embodiment, R^(W) is CN and T is R^(A).

In one embodiment, R^(W) is CN and Y is R^(A).

In one embodiment, R^(W) is CN and X is R^(A).

In one embodiment, R^(W) is CN and W is R^(A).

In one embodiment, R^(W) is CN and V is R^(A).

In one embodiment, A^(I) and A^(II) is CF₃.

In one embodiment, A^(I) and A^(III) is CF₃.

In one embodiment, A^(I) and A^(IV) is CF₃.

In one embodiment, A^(I) and A^(V) is CF₃.

In one embodiment, A^(II) and A^(III) is CF₃.

In one embodiment, A^(II) and A^(IV) is CF₃.

In a further embodiment of the invention, R^(I) is independently fromeach other selected from the group consisting of H, methyl, and phenyl,wherein phenyl is optionally substituted with one or more substituentsR⁶.

In a further embodiment of the invention, R^(I) is independently fromeach other selected from the group consisting of H, methyl, and phenyl.

In a further embodiment of the invention, R^(I) is H at each occurrence.

In a further embodiment of the invention, each of the two secondchemical moieties at each occurrence, independently from another,comprise or consist of a structure of formula IIa:

wherein # and R^(a) are as defined above.

In a further embodiment of the invention, R^(a) is at each occurrenceindependently from another selected from the group consisting of:

-   H,-   Me,-   ^(i)Pr,-   ^(t)Bu,-   CN,-   CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   and N(Ph)₂.

In a further embodiment of the invention, R^(a) is at each occurrenceindependently from another selected from the group consisting of:

-   H,-   Me,-   ^(i)Pr,-   ^(t)Bu,-   CN,-   CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.

In a further embodiment of the invention, R^(a) is at each occurrenceindependently from another selected from the group consisting of:

-   H,-   Me,-   ^(t)Bu,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.

In a further embodiment of the invention, R^(a) is H at each occurrence.

In a further embodiment of the invention, each of the two secondchemical moieties independently from another comprise or consist of astructure of Formula IIb, a structure of Formula IIb-2, a structure ofFormula IIb-3 or a structure of Formula IIb-4:

wherein

R^(b) is at each occurrence independently from another selected from thegroup consisting of:

deuterium,

N(R⁵)₂,

OR⁵,

Si(R⁵)₃,

B(OR⁵)₂,

OSO₂R⁵,

CF₃,

CN,

F,

Br,

I,

C₁-C₄₀-alkyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₁-C₄₀-alkoxy,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₁-C₄₀-thioalkoxy,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₂-C₄₀-alkenyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₂-C₄₀-alkynyl,

-   -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;

C₆-C₆₀-aryl,

-   -   which is optionally substituted with one or more substituents        R⁵; and

C₃-C₅₇-heteroaryl,

-   -   which is optionally substituted with one or more substituents        R⁵.

Apart from that, the aforementioned definitions apply.

In another embodiment of the invention, each of the two second chemicalmoieties at each occurrence, independently from another, comprise orconsist of a structure of formula IIc, a structure of formula IIc-2, astructure of formula IIc-3 or a structure of formula IIc-4:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, R^(b) is at each occurrenceindependently from another selected from the group consisting of:

-   Me,-   ^(i)Pr,-   ^(t)Bu,-   CN,-   CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph; and-   N(Ph)₂.

In a further embodiment of the invention, R^(b) is at each occurrenceindependently from another selected from the group consisting of:

-   Me,-   ^(i)Pr,-   ^(t)Bu,-   CN,-   CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph, and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.

In a further embodiment of the invention, R^(b) is at each occurrenceindependently from another selected from the group consisting of:

-   Me,-   ^(t)Bu,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.

In the following, exemplary embodiments of the second chemical moietyare shown:

wherein for #, Z, R^(a), R³, R⁴ and R⁵, the aforementioned definitionsapply.

In one embodiment, R^(a) and R⁵ is at each occurrence independently fromanother selected from the group consisting of hydrogen (H), methyl (Me),i-propyl (CH(CH₃)₂) (^(i)Pr), t-butyl (^(t)Bu), phenyl (Ph), CN, CF₃,and diphenylamine (NPh₂).

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of formula IIIA, formula IIIB or formula IIIC:

wherein the aforementioned definitions apply.

In a preferred embodiment of the invention, the organic moleculescomprise or consist of a structure of formula IIIA.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula III-1,formula III-2, formula III-3, formula III-4, formula III-5 and formulaIII-6:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula IIIa-1 andformula IIIa-2:

wherein

R^(c) is at each occurrence independently from another selected from thegroup consisting of:

-   Me,-   ^(i)Pr,-   ^(t)Bu,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph;

and N(Ph)₂.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula IIIb-1 andformula IIIb-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula IIIc-1 andformula IIIc-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula IIId-1 andformula IIId-2:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of formula IVA, formula IVB or formula IVC:

wherein the aforementioned definitions apply.

In a preferred embodiment of the invention, the organic moleculescomprise or consist of a structure of formula IVA.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula IV-1,formula IV-2, formula IV-3, formula IV-4, formula IV-5 and formula IV-6:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula IVa-1 andformula IVa-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula IVb-1 andformula IVb-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula IVc-1 andformula IVc-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula IVd-1 andformula IVd-2:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of formula VA, formula VB or formula VC:

wherein the aforementioned definitions apply.

In a preferred embodiment of the invention, the organic moleculescomprise or consist of a structure of formula VA.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula V-1,formula V-2, formula V-3, formula V-4, formula V-5 and formula V-6:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula Va-1 andformula Va-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula Vb-1 andformula Vb-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula Vc-1 andformula Vc-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula Vd-1 andformula Vd-2:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of formula VIA, formula VIB or formula VIC:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula VI-1,formula VI-2, formula VI-3, formula VI-4, formula VI-5 and formula VI-6:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula VIa-1 andformula VIa-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula VIb-1 andformula VIb-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula VIc-1 andformula VIc-2:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of formula VId-1 andformula VId-2:

wherein the aforementioned definitions apply.

In one embodiment of the invention R^(c) is at each occurrenceindependently from another selected from the group consisting of:

-   Me,-   ^(i)Pr,-   ^(t)Bu,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph.

As used throughout the present application, the terms “aryl” and“aromatic” may be understood in the broadest sense as any mono-, bi- orpolycyclic aromatic moieties. Accordingly, an aryl group contains 6 to60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromaticring atoms, of which at least one is a heteroatom. Notwithstanding,throughout the application the number of aromatic ring atoms may begiven as subscripted number in the definition of certain substituents.In particular, the heteroaromatic ring includes one to threeheteroatoms. Again, the terms “heteroaryl” and “heteroaromatic” may beunderstood in the broadest sense as any mono-, bi- or polycyclichetero-aromatic moieties that include at least one heteroatom. Theheteroatoms may at each occurrence be the same or different and beindividually selected from the group consisting of N, O and S.Accordingly, the term “arylene” refers to a divalent substituent thatbears two binding sites to other molecular structures and therebyserving as a linker structure. In case, a group in the exemplaryembodiments is defined differently from the definitions given here, forexample, the number of aromatic ring atoms or number of heteroatomsdiffers from the given definition, the definition in the exemplaryembodiments is to be applied. According to the invention, a condensed(annulated) aromatic or heteroaromatic polycycle is built of two or moresingle aromatic or heteroaromatic cycles, which formed the polycycle viaa condensation reaction.

In particular, as used throughout the present application the term arylgroup or heteroaryl group comprises groups which can be bound via anyposition of the aromatic or heteroaromatic group, derived from benzene,naphthaline, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene,perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene,pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran,thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole,indole, isoindole, carbazole, pyridine, quinoline, isoquinoline,acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline,benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole,imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole,pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole,benzoxazole, napthooxazole, anthroxazol, phenanthroxazol, isoxazole,1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine,pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine,phenazine, naphthyridine, carboline, benzocarboline, phenanthroline,1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole,1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine,pteridine, indolizine and benzothiadiazole or combinations of theabovementioned groups.

As used throughout the present application the term cyclic group may beunderstood in the broadest sense as any mono-, bi- or polycyclicmoieties.

As used throughout the present application, the term biphenyl as asubstituent may be understood in the broadest sense as ortho-biphenyl,meta-biphenyl, or para-biphenyl, wherein ortho, meta and para is definedin regard to the binding site to another chemical moiety.

As used throughout the present application, the term alkyl group may beunderstood in the broadest sense as any linear, branched, or cyclicalkyl substituent. In particular, the term alkyl comprises thesubstituents methyl (Me), ethyl (Et), n-propyl (^(n)Pr), i-propyl(^(i)Pr), cyclopropyl, n-butyl (^(n)Bu), i-butyl (^(i)Bu), s-butyl(^(s)Bu), t-butyl (^(t)Bu), cyclobutyl, 2-methylbutyl, n-pentyl,s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl,t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl,2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl,1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl,1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]-octyl, 2-(2,6-dimethyl)octyl,3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluorethyl,1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl,1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl,1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl,1,1-dimethyl-n-hexadec-1-yl, 1,1-dimethyl-n-octadec-1-yl,1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl,1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec-1-yl,1,1-diethyl-n-tetradec-1-yl, 1,1-diethyln-n-hexadec-1-yl,1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohex-1-yl,1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl,1-(n-octyl)-cyclohex-1-yl and 1-(n-decyl)-cyclohex-1-yl.

As used throughout the present application, the term alkenyl compriseslinear, branched, and cyclic alkenyl substituents. The term alkenylgroup exemplarily comprises the substituents ethenyl, propenyl, butenyl,pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl,octenyl, cyclooctenyl or cyclooctadienyl.

As used throughout the present application, the term alkynyl compriseslinear, branched, and cyclic alkynyl substituents. The term alkynylgroup exemplarily comprises ethynyl, propynyl, butynyl, pentynyl,hexynyl, heptynyl or octynyl.

As used throughout the present application, the term alkoxy compriseslinear, branched, and cyclic alkoxy substituents. The term alkoxy groupexemplarily comprises methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy,i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.

As used throughout the present application, the term thioalkoxycomprises linear, branched, and cyclic thioalkoxy substituents, in whichthe O of the exemplarily alkoxy groups is replaced by S.

As used throughout the present application, the terms “halogen” and“halo” may be understood in the broadest sense as being preferablyfluorine, chlorine, bromine or iodine.

Whenever hydrogen (H) is mentioned herein, it could also be replaced bydeuterium at each occurrence.

It is understood that when a molecular fragment is described as being asubstituent or otherwise attached to another moiety, its name may bewritten as if it were a fragment (e.g. naphtyl, dibenzofuryl) or as ifit were the whole molecule (e.g. naphthalene, dibenzofuran).

As used herein, these different ways of designating a substituent orattached fragment are considered to be equivalent.

In one embodiment, the organic molecules according to the invention havean excited state lifetime of not more than 150 μs, of not more than 100μs, in particular of not more than 50 μs, more preferably of not morethan 10 μs or not more than 7 μs in a film of poly(methyl methacrylate)(PMMA) with 10% by weight of organic molecule at room temperature.

In one embodiment of the invention, the organic molecules according tothe invention represent thermally-activated delayed fluorescence (TADF)emitters, which exhibit a ΔE_(ST) value, which corresponds to the energydifference between the first excited singlet state (S1) and the firstexcited triplet state (T1), of less than 5000 cm⁻¹, preferably less than3000 cm⁻¹, more preferably less than 1500 cm⁻¹, even more preferablyless than 1000 cm⁻¹ or even less than 500 cm⁻¹.

In a further embodiment of the invention, the organic moleculesaccording to the invention have an emission peak in the visible ornearest ultraviolet range, i.e., in the range of a wavelength of from380 to 800 nm, with a full width at half maximum of less than 0.50 eV,preferably less than 0.48 eV, more preferably less than 0.45 eV, evenmore preferably less than 0.43 eV or even less than 0.40 eV in a film ofpoly(methyl methacrylate) (PMMA) with 10% by weight of organic moleculeat room temperature.

In a further embodiment of the invention, the organic moleculesaccording to the invention have a “blue material index” (BMI),calculated by dividing the photoluminescence quantum yield (PLQY) in %by the CIEy color coordinate of the emitted light, of more than 150, inparticular more than 200, preferably more than 250, more preferably ofmore than 300 or even more than 500.

Orbital and excited state energies can be determined either by means ofexperimental methods or by calculations employing quantum-chemicalmethods, in particular density functional theory calculations. Theenergy of the highest occupied molecular orbital E^(HOMO) is determinedby methods known to the person skilled in the art from cyclicvoltammetry measurements with an accuracy of 0.1 eV. The energy of thelowest unoccupied molecular orbital E^(LUMO) is calculated asE^(HOMO)+E^(gap), wherein E^(gap) is determined as follows: For hostcompounds, the onset of the emission spectrum of a film with 10% byweight of host in poly(methyl methacrylate) (PMMA) is used as E^(gap),unless stated otherwise. For emitter molecules, E^(gap) is determined asthe energy at which the excitation and emission spectra of a film with10% by weight of emitter in PMMA cross.

The energy of the first excited triplet state T1 is determined from theonset of the emission spectrum at low temperature, typically at 77 K.For host compounds, where the first excited singlet state and the lowesttriplet state are energetically separated by >0.4 eV, thephosphorescence is usually visible in a steady-state spectrum in2-Me-THF. The triplet energy can thus be determined as the onset of thephosphorescence spectrum. For TADF emitter molecules, the energy of thefirst excited triplet state T1 is determined from the onset of thedelayed emission spectrum at 77 K, if not otherwise stated measured in afilm of PMMA with 10% by weight of emitter. Both for host and emittercompounds, the energy of the first excited singlet state S1 isdetermined from the onset of the emission spectrum, if not otherwisestated measured in a film of PMMA with 10% by weight of host or emittercompound.

The onset of an emission spectrum is determined by computing theintersection of the tangent to the emission spectrum with the x-axis.The tangent to the emission spectrum is set at the high-energy side ofthe emission band and at the point at half maximum of the maximumintensity of the emission spectrum.

A further aspect of the invention relates to a method for preparingorganic molecules of the invention (with an optional subsequentreaction), wherein a bromo-fluorobenzonitrile, which is substituted withthree R², is used as a reactant:

According to the invention, in the reaction for the synthesis of E1, aboronic acid or an equivalent boronic acid ester can be used instead ofa boronic pinacol ester. Exemplary boronic acid esters or boronic acidsare 2-chloro-6-fluorophenylboronic ester or acid,2-chloro-5-fluorophenylboronic ester or acid,2-chloro-4-fluorophenylboronic ester or acid,3-chloro-6-fluorophenylboronic ester or acid,3-chloro-5-fluorophenylboronic ester or acid,3-chloro-4-fluorophenylboronic ester or acid,4-chloro-6-fluorophenylboronic ester or acid and4-chloro-5-fluorophenylboronic ester or acid.

Typically, Pd₂(dba)₃ (tris(dibenzylideneacetone)dipalladium(0)) is usedas a Pd catalyst, but alternatives are known in the art. For example,the ligand may be selected from S-Phos([2-dicyclohexylphoshino-2′,6′-dimethoxy-1,1′-biphenyl]), X-Phos(2-(dicyclohexylphosphino)-2″,4″,6″-triisopropylbiphenyl), and P(Cy)₃(tricyclohexylphosphine). The salt may, for example, be selected fromtribasic potassium phosphate and potassium acetate and the solvent maybe a pure solvent, such as toluene or dioxane, or a mixture, such astoluene/dioxane/water or dioxane/toluene. A person of skill in the artis able to determine which combination of Pd catalyst, ligand, salt andsolvent will give high reaction yields.

For the reaction of a nitrogen heterocycle in a nucleophilic aromaticsubstitution with an aryl halide, preferably an aryl fluoride, typicalconditions include the use of a base, such as tribasic potassiumphosphate or sodium hydride, for example, in an aprotic polar solvent,such as dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF), forexample.

An alternative synthesis route comprises the introduction of a nitrogenheterocycle via copper- or palladium-catalyzed coupling to an arylhalide or aryl pseudohalide, preferably an aryl bromide, an aryl iodide,aryl triflate or an aryl tosylate.

A further aspect of the invention relates to the use of an organicmolecule according to the invention as a luminescent emitter or as anabsorber, and/or as a host material and/or as an electron transportmaterial, and/or as a hole injection material, and/or as a hole blockingmaterial in an optoelectronic device.

The optoelectronic device, also referred to as optoelectronic device,may be understood in the broadest sense as any device based on organicmaterials that is suitable for emitting light in the visible or nearestultraviolet (UV) range, i.e., in the range of a wavelength of from 380to 800 nm. More preferably, the optoelectronic device may be able toemit light in the visible range, i.e., of from 400 nm to 800 nm.

In the context of such use, the organic optoelectronic device is moreparticularly selected from the group consisting of:

-   -   organic light-emitting diodes (OLEDs),    -   light-emitting electrochemical cells,    -   OLED sensors, especially in gas and vapour sensors not        hermetically externally shielded,    -   organic diodes,    -   organic solar cells,    -   organic transistors,    -   organic field-effect transistors,    -   organic lasers and    -   down-conversion elements.

In a preferred embodiment in the context of such use, the optoelectronicdevice is a device selected from the group consisting of an organiclight emitting diode (OLED), a light emitting electrochemical cell(LEC), and a light-emitting transistor.

In the case of the use, the fraction of the organic molecule accordingto the invention in the emission layer in an organic optoelectronicdevice, more particularly in an OLED, is 1% to 99% by weight, moreparticularly 5% to 80% by weight. In an alternative embodiment, theproportion of the organic molecule in the emission layer is 100% byweight.

In one embodiment, the light-emitting layer comprises not only theorganic molecules according to the invention, but also a host materialwhose triplet (T1) and singlet (S1) energy levels are energeticallyhigher than the triplet (T1) and singlet (S1) energy levels of theorganic molecule.

A further aspect of the invention relates to a composition comprising orconsisting of:

-   (a) at least one organic molecule according to the invention, in    particular in the form of an emitter and/or a host, and-   (b) one or more emitter and/or host materials, which differ from the    organic molecule according to the invention and-   (c) optional one or more dyes and/or one or more solvents.

In one embodiment, the light-emitting layer comprises (or essentiallyconsists of) a composition comprising or consisting of:

-   (a) at least one organic molecule according to the invention, in    particular in the form of an emitter and/or a host, and-   (b) one or more emitter and/or host materials, which differ from the    organic molecule according to the invention and-   (c) optional one or more dyes and/or one or more solvents.

In a particular embodiment, the light-emitting layer EML comprises (oressentially consists of) a composition comprising or consisting of:

-   (i) 1-50% by weight, preferably 5-40% by weight, in particular    10-30% by weight, of one or more organic molecules according to the    invention;-   (ii) 5-99% by weight, preferably 30-94.9% by weight, in particular    40-89% by weight, of at least one host compound H; and-   (iii) optionally 0-94% by weight, preferably 0.1-65% by weight, in    particular 1-50% by weight, of at least one further host compound D    with a structure differing from the structure of the molecules    according to the invention; and-   (iv) optionally 0-94% by weight, preferably 0-65% by weight, in    particular 0-50% by weight, of a solvent; and-   (v) optionally 0-30% by weight, in particular 0-20% by weight,    preferably 0-5% by weight, of at least one further emitter molecule    F with a structure differing from the structure of the molecules    according to the invention.

Preferably, energy can be transferred from the host compound H to theone or more organic molecules according to the invention, in particulartransferred from the first excited triplet state T1(H) of the hostcompound H to the first excited triplet state T1(E) of the one or moreorganic molecules according to the invention E and/or from the firstexcited singlet state S1(H) of the host compound H to the first excitedsinglet state S1(E) of the one or more organic molecules according tothe invention E.

In a further embodiment, the light-emitting layer EML comprises (oressentially consists of) a composition comprising or consisting of:

-   (i) 1-50% by weight, preferably 5-40% by weight, in particular    10-30% by weight, of one organic molecule according to the    invention;-   (ii) 5-99% by weight, preferably 30-94.9% by weight, in particular    40-89% by weight, of one host compound H; and-   (iii) optionally 0-94% by weight, preferably 0.1-65% by weight, in    particular 1-50% by weight, of at least one further host compound D    with a structure differing from the structure of the molecules    according to the invention; and-   (iv) optionally 0-94% by weight, preferably 0-65% by weight, in    particular 0-50% by weight, of a solvent; and-   (v) optionally 0-30% by weight, in particular 0-20% by weight,    preferably 0-5% by weight, of at least one further emitter molecule    F with a structure differing from the structure of the molecules    according to the invention.

In one embodiment, the host compound H has a highest occupied molecularorbital HOMO(H) having an energy E^(HOMO)(H) in the range of from −5 to−6.5 eV and the at least one further host compound D has a highestoccupied molecular orbital HOMO(D) having an energy E^(HOMO)(D), whereinE^(HOMO)(H)>E^(HOMO)(D).

In a further embodiment, the host compound H has a lowest unoccupiedmolecular orbital LUMO(H) having an energy E^(LUMO)(H) and the at leastone further host compound D has a lowest unoccupied molecular orbitalLUMO(D) having an energy E^(LUMO)(D), wherein E^(LUMO)(H)>E^(LUMO)(D).

In one embodiment, the host compound H has a highest occupied molecularorbital HOMO(H) having an energy E^(HOMO)(H) and a lowest unoccupiedmolecular orbital LUMO(H) having an energy E^(LUMO)(H), and

-   -   the at least one further host compound D has a highest occupied        molecular orbital HOMO(D) having an energy E^(HOMO)(D) and a        lowest unoccupied molecular orbital LUMO(D) having an energy        E^(LUMO)(D),    -   the organic molecule according to the invention E has a highest        occupied molecular orbital HOMO(E) having an energy E^(HOMO)(E)        and a lowest unoccupied molecular orbital LUMO(E) having an        energy E^(LUMO)(E),

wherein

E^(HOMO)(H)>E^(HOMO)(D) and the difference between the energy level ofthe highest occupied molecular orbital HOMO(E) of the organic moleculeaccording to the invention E (E^(HOMO)(E)) and the energy level of thehighest occupied molecular orbital HOMO(H) of the host compound H(E^(HOMO)(H)) is between −0.5 eV and 0.5 eV, more preferably between−0.3 eV and 0.3 eV, even more preferably between −0.2 eV and 0.2 eV oreven between −0.1 eV and 0.1 eV; and

E^(LUMO)(H)>E^(LUMO)(D) and the difference between the energy level ofthe lowest unoccupied molecular orbital LUMO(E) of the organic moleculeaccording to the invention E (E^(LUMO)(E)) and the lowest unoccupiedmolecular orbital LUMO(D) of the at least one further host compound D(E^(LUMO)(D)) is between −0.5 eV and 0.5 eV, more preferably between−0.3 eV and 0.3 eV, even more preferably between −0.2 eV and 0.2 eV oreven between −0.1 eV and 0.1 eV.

In a further aspect, the invention relates to an organic optoelectronicdevice comprising an organic molecule or a composition of the typedescribed here, more particularly in the form of a device selected fromthe group consisting of organic light-emitting diode (OLED),light-emitting electrochemical cell, OLED sensor, more particularly gasand vapour sensors not hermetically externally shielded, organic diode,organic solar cell, organic transistor, organic field-effect transistor,organic laser and down-conversion element.

In a preferred embodiment, the optoelectronic device is a deviceselected from the group consisting of an organic light emitting diode(OLED), a light emitting electrochemical cell (LEC), and alight-emitting transistor.

In one embodiment of the organic optoelectronic device of the invention,the organic molecule according to the invention E is used as emissionmaterial in a light-emitting layer EML.

In one embodiment of the organic optoelectronic device of the invention,the light-emitting layer EML consists of the composition according tothe invention described here.

Exemplarily, when the optoelectronic device is an OLED, it may have thefollowing layer structure:

1. substrate

2. anode layer A

3. hole injection layer, HIL

4. hole transport layer, HTL

5. electron blocking layer, EBL

6. emitting layer, EML

7. hole blocking layer, HBL

8. electron transport layer, ETL

9. electron injection layer, EIL

10. cathode layer,

wherein the OLED comprises each layer selected from the group of HIL,HTL, EBL, HBL, ETL, and EIL only optionally, different layers may bemerged and the OLED may comprise more than one layer of each layer typedefined above.

Furthermore, the optoelectronic device may optionally comprise one ormore protective layers protecting the device from damaging exposure toharmful species in the environment including, for example, moisture,vapor and/or gases.

In one embodiment of the invention, the optoelectronic device is anOLED, which has the following inverted layer structure:

1. substrate

2. cathode layer

3. electron injection layer, EIL

4. electron transport layer, ETL

5. hole blocking layer, HBL

6. emitting layer, B

7. electron blocking layer, EBL

8. hole transport layer, HTL

9. hole injection layer, HIL

10. anode layer A

wherein the OLED comprises each layer selected from the group of HIL,HTL, EBL, HBL, ETL, and EIL only optionally, different layers may bemerged and the OLED may comprise more than one layer of each layer typesdefined above.

In one embodiment of the invention, the optoelectronic device is anOLED, which may exhibit stacked architecture. In this architecture,contrary to the typical arrangement, where the OLEDs are placed side byside, the individual units are stacked on top of each other.

Blended light may be generated with OLEDs exhibiting a stackedarchitecture, in particular white light may be generated by stackingblue, green and red OLEDs. Furthermore, the OLED exhibiting a stackedarchitecture may optionally comprise a charge generation layer (CGL),which is typically located between two OLED subunits and typicallyconsists of a n-doped and p-doped layer with the n-doped layer of oneCGL being typically located closer to the anode layer.

In one embodiment of the invention, the optoelectronic device is anOLED, which comprises two or more emission layers between anode andcathode. In particular, this so-called tandem OLED comprises threeemission layers, wherein one emission layer emits red light, oneemission layer emits green light and one emission layer emits bluelight, and optionally may comprise further layers such as chargegeneration layers, blocking or transporting layers between theindividual emission layers. In a further embodiment, the emission layersare adjacently stacked. In a further embodiment, the tandem OLEDcomprises a charge generation layer between each two emission layers. Inaddition, adjacent emission layers or emission layers separated by acharge generation layer may be merged.

The substrate may be formed by any material or composition of materials.Most frequently, glass slides are used as substrates. Alternatively,thin metal layers (e.g., copper, gold, silver or aluminum films) orplastic films or slides may be used. This may allow a higher degree offlexibility. The anode layer A is mostly composed of materials allowingto obtain an (essentially) transparent film. As at least one of bothelectrodes should be (essentially) transparent in order to allow lightemission from the OLED, either the anode layer A or the cathode layer Cis transparent. Preferably, the anode layer A comprises a large contentor even consists of transparent conductive oxides (TCOs). Such anodelayer A may, for example, comprise indium tin oxide, aluminum zincoxide, fluorine doped tin oxide, indium zinc oxide, PbO, SnO, zirconiumoxide, molybdenum oxide, vanadium oxide, wolfram oxide, graphite, dopedSi, doped Ge, doped GaAs, doped polyaniline, doped polypyrrol and/ordoped polythiophene.

The anode layer A (essentially) may consist of indium tin oxide (ITO)(e.g., (InO₃)_(0.9)(SnO₂)_(0.1)). The roughness of the anode layer Acaused by the transparent conductive oxides (TCOs) may be compensated byusing a hole injection layer (HIL). Further, the HIL may facilitate theinjection of quasi charge carriers (i.e., holes) in that the transportof the quasi charge carriers from the TCO to the hole transport layer(HTL) is facilitated. The hole injection layer (HIL) may comprisepoly-3,4-ethylendioxy thiophene (PEDOT), polystyrene sulfonate (PSS),MoO₂, V₂O₅, CuPC or CuI, in particular a mixture of PEDOT and PSS. Thehole injection layer (HIL) may also prevent the diffusion of metals fromthe anode layer A into the hole transport layer (HTL). The HIL mayexemplarily comprise PEDOT:PSS (poly-3,4-ethylendioxythiophene:polystyrene sulfonate), PEDOT (poly-3,4-ethylendioxythiophene), mMTDATA (4,4′,4″-tris[phenyl(m-tolyl)amino]triphenylamine),Spiro-TAD (2,2′,7,7′-tetrakis(n,n-diphenylamino)-9,9′-spirobifluorene),DNTPD (N1,N1′-(biphenyl-4,4′-diyl)bis(NI-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine), NPB(N,N′-nis-(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine),NPNPB (N,N′-diphenyl-N,N′-di-[4-(N,N-diphenyl-amino)phenyl]benzidine),MeO-TPD (N,N,N′,N′-tetrakis(4-methoxyphenyl)benzidine), HAT-CN(1,4,5,8,9,11-hexaazatriphenylen-hexacarbonitrile) and/or Spiro-NPD(N,N′-diphenyl-N,N′-bis-(1-naphthyl)-9,9′-spirobifluorene-2,7-diamine).

Adjacent to the anode layer A or hole injection layer (HIL), a holetransport layer (HTL) is typically located. Herein, any hole transportcompound may be used. Exemplarily, electron-rich heteroaromaticcompounds such as triarylamines and/or carbazoles may be used as holetransport compound. The HTL may decrease the energy barrier between theanode layer A and the light-emitting layer EML. The hole transport layer(HTL) may also be an electron blocking layer (EBL). Preferably, holetransport compounds bear comparably high energy levels of their tripletstates T1. For example, the hole transport layer (HTL) may comprise astar-shaped heterocycle such as tris(4-carbazoyl-9-ylphenyl)amine(TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), [alpha]-NPD(poly(4-butylphenyl-diphenyl-amine)), TAPC(4,4′-cyclohexyliden-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA(4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD,NPB, NPNPB, MeO-TPD, HAT-CN and/or TrisPcz(9,9′-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9′H-3,3′-bicarbazole).In addition, the HTL may comprise a p-doped layer, which may be composedof an inorganic or organic dopant in an organic hole-transportingmatrix. Transition metal oxides such as vanadium oxide, molybdenum oxideor tungsten oxide may exemplarily be used as inorganic dopant.Tetrafluorotetracyanoquinodimethane (F₄-TCNQ),copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes mayexemplarily be used as organic dopant.

The EBL may exemplarily comprise mCP (1,3-bis(carbazol-9-yl)benzene),TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi(9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and/orDCB (N,N′-dicarbazolyl-1,4-dimethylbenzene).

Adjacent to the hole transport layer (HTL), typically, thelight-emitting layer EML is located. The light-emitting layer EMLcomprises at least one light emitting molecule. Particularly, the EMLcomprises at least one light emitting molecule according to theinvention E. In one embodiment, the light-emitting layer comprises onlythe organic molecules according to the invention. Typically, the EMLadditionally comprises one or more host materials H. Exemplarily, thehost material H is selected from CBP (4,4′-Bis-(N-carbazolyl)-biphenyl),mCP, mCBP Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88(dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO(bis[2-(diphenylphosphino)phenyl] ether oxide),9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T(2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T(2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and/or TST(2,4,6-tris(9,9′-spirobifluorene-2-yl)-1,3,5-triazine). The hostmaterial H typically should be selected to exhibit first triplet (T1)and first singlet (S1) energy levels, which are energetically higherthan the first triplet (T1) and first singlet (S1) energy levels of theorganic molecule.

In one embodiment of the invention, the EML comprises a so-calledmixed-host system with at least one hole-dominant host and oneelectron-dominant host. In a particular embodiment, the EML comprisesexactly one light emitting organic molecule according to the inventionand a mixed-host system comprising T2T as electron-dominant host and ahost selected from CBP, mCP, mCBP,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole as hole-dominanthost. In a further embodiment the EML comprises 50-80% by weight,preferably 60-75% by weight of a host selected from CBP, mCP, mCBP,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole; 10-45% by weight,preferably 15-30% by weight of T2T and 5-40% by weight, preferably10-30% by weight of light emitting molecule according to the invention.

Adjacent to the light-emitting layer EML, an electron transport layer(ETL) may be located. Herein, any electron transporter may be used.Exemplarily, electron-poor compounds such as, e.g., benzimidazoles,pyridines, triazoles, oxadiazoles (e.g., 1,3,4-oxadiazole),phosphinoxides and sulfone, may be used. An electron transporter mayalso be a star-shaped heterocycle such as1,3,5-tri(1-phenyl-H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL maycomprise NBphen(2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq₃(Aluminum-tris(8-hydroxyquinoline)), TSPO1(diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2(2,7-di(2,2′-bipyridin-5-yl)triphenyle), Sif87(dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88(dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB(1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene) and/or BTB(4,4′-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-biphenyl). Optionally,the ETL may be doped with materials such as Liq. The electron transportlayer (ETL) may also block holes or a holeblocking layer (HBL) isintroduced. The HBL may exemplarily comprise BCP(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline=Bathocuproine), BAlq(bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen(2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq₃(Aluminum-tris(8-hydroxyquinoline)), TSPO1(diphenyl-4-triphenylsilylphenyl-phosphinoxide), T2T(2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T(2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), TST(2,4,6-tris(9,9′-spirobifluorene-2-yl)-1,3,5-triazine), and/or TCB/TCP(1,3,5-tris(N-carbazolyl)benzol/1,3,5-tris(carbazol)-9-yl) benzene).

Adjacent to the electron transport layer (ETL), a cathode layer C may belocated. Exemplarily, the cathode layer C may comprise or may consist ofa metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In,W, or Pd) or a metal alloy. For practical reasons, the cathode layer mayalso consist of (essentially) intransparent metals such as Mg, Ca or Al.Alternatively or additionally, the cathode layer C may also comprisegraphite and or carbon nanotubes (CNTs). Alternatively, the cathodelayer C may also consist of nanoscalic silver wires.

An OLED may further, optionally, comprise a protection layer between theelectron transport layer (ETL) and the cathode layer C (which may bedesignated as electron injection layer (EIL)). This layer may compriselithium fluoride, cesium fluoride, silver, Liq(8-hydroxyquinolinolatolithium), Li₂O, BaF₂, MgO and/or NaF.

Optionally, also the electron transport layer (ETL) and/or a holeblocking layer (HBL) may comprise one or more host compounds H.

In order to modify the emission spectrum and/or the absorption spectrumof the light-emitting layer EML further, the light-emitting layer EMLmay further comprise one or more further emitter molecules F. Such anemitter molecule F may be any emitter molecule known in the art.Preferably such an emitter molecule F is a molecule with a structurediffering from the structure of the molecules according to the inventionE. The emitter molecule F may optionally be a TADF emitter.Alternatively, the emitter molecule F may optionally be a fluorescentand/or phosphorescent emitter molecule which is able to shift theemission spectrum and/or the absorption spectrum of the light-emittinglayer EML. Exemplarily, the triplet and/or singlet excitons may betransferred from the organic emitter molecule according to the inventionto the emitter molecule F before relaxing to the ground state S0 byemitting light typically red-shifted in comparison to the light emittedby an organic molecule. Optionally, the emitter molecule F may alsoprovoke two-photon effects (i.e., the absorption of two photons of halfthe energy of the absorption maximum).

Optionally, an optoelectronic device (e.g., an OLED) may exemplarily bean essentially white optoelectronic device. Exemplarily such whiteoptoelectronic device may comprise at least one (deep) blue emittermolecule and one or more emitter molecules emitting green and/or redlight. Then, there may also optionally be energy transmittance betweentwo or more molecules as described above.

As used herein, if not defined more specifically in the particularcontext, the designation of the colors of emitted and/or absorbed lightis as follows:

violet: wavelength range of >380-420 nm;

deep blue: wavelength range of >420-480 nm;

sky blue: wavelength range of >480-500 nm;

green: wavelength range of >500-560 nm;

yellow: wavelength range of >560-580 nm;

orange: wavelength range of >580-620 nm;

red: wavelength range of >620-800 nm.

With respect to emitter molecules, such colors refer to the emissionmaximum. Therefore, exemplarily, a deep blue emitter has an emissionmaximum in the range of from >420 to 480 nm, a sky blue emitter has anemission maximum in the range of from >480 to 500 nm, a green emitterhas an emission maximum in a range of from >500 to 560 nm, a red emitterhas an emission maximum in a range of from >620 to 800 nm.

A deep blue emitter may preferably have an emission maximum of below 480nm, more preferably below 470 nm, even more preferably below 465 nm oreven below 460 nm. It will typically be above 420 nm, preferably above430 nm, more preferably above 440 nm or even above 450 nm.

Accordingly, a further aspect of the present invention relates to anOLED, which exhibits an external quantum efficiency at 1000 cd/m² ofmore than 8%, more preferably of more than 10%, more preferably of morethan 13%, even more preferably of more than 15% or even more than 20%and/or exhibits an emission maximum between 420 nm and 500 nm,preferably between 430 nm and 490 nm, more preferably between 440 nm and480 nm, even more preferably between 450 nm and 470 nm and/or exhibits aLT80 value at 500 cd/m² of more than 100 h, preferably more than 200 h,more preferably more than 400 h, even more preferably more than 750 h oreven more than 1000 h. Accordingly, a further aspect of the presentinvention relates to an OLED, whose emission exhibits a CIEy colorcoordinate of less than 0.45, preferably less than 0.30, more preferablyless than 0.20 or even more preferably less than 0.15 or even less than0.10.

A further aspect of the present invention relates to an OLED, whichemits light at a distinct color point. According to the presentinvention, the OLED emits light with a narrow emission band (small fullwidth at half maximum (FWHM)). In one aspect, the OLED according to theinvention emits light with a FWHM of the main emission peak of less than0.50 eV, preferably less than 0.48 eV, more preferably less than 0.45eV, even more preferably less than 0.43 eV or even less than 0.40 eV.

A further aspect of the present invention relates to an OLED, whichemits light with CIEx and CIEy color coordinates close to the CIEx(=0.131) and CIEy (=0.046) color coordinates of the primary color blue(CIEx=0.131 and CIEy=0.046) as defined by ITU-R Recommendation BT.2020(Rec. 2020) and thus is suited for the use in Ultra High Definition(UHD) displays, e.g. UHD-TVs. Accordingly, a further aspect of thepresent invention relates to an OLED, whose emission exhibits a CIExcolor coordinate of between 0.02 and 0.30, preferably between 0.03 and0.25, more preferably between 0.05 and 0.20 or even more preferablybetween 0.08 and 0.18 or even between 0.10 and 0.15 and/or a a CIEycolor coordinate of between 0.00 and 0.45, preferably between 0.01 and0.30, more preferably between 0.02 and 0.20 or even more preferablybetween 0.03 and 0.15 or even between 0.04 and 0.10.

In a further aspect, the invention relates to a method for producing anoptoelectronic component. In this case an organic molecule of theinvention is used.

The optoelectronic device, in particular the OLED according to thepresent invention can be manufactured by any means of vapor depositionand/or liquid processing. Accordingly, at least one layer is

-   -   prepared by means of a sublimation process,    -   prepared by means of an organic vapor phase deposition process,    -   prepared by means of a carrier gas sublimation process,    -   solution processed or printed.

The methods used to manufacture the optoelectronic device, in particularthe OLED according to the present invention are known in the art. Thedifferent layers are individually and successively deposited on asuitable substrate by means of subsequent deposition processes. Theindividual layers may be deposited using the same or differingdeposition methods.

Vapor deposition processes exemplarily comprise thermal (co)evaporation,chemical vapor deposition and physical vapor deposition. For activematrix OLED display, an AMOLED backplane is used as substrate. Theindividual layer may be processed from solutions or dispersionsemploying adequate solvents. Solution deposition process exemplarilycomprise spin coating, dip coating and jet printing. Liquid processingmay optionally be carried out in an inert atmosphere (e.g., in anitrogen atmosphere) and the solvent may optionally be completely orpartially removed by means known in the state of the art.

EXAMPLES General Synthesis Scheme I

General Procedure for Synthesis AAV1

3-bromo-4-fluorobenzonitrile (1.00 equivalents),4-chloro-2-fluorophenylboronic ester (1.2 equivalents), Pd₂(dba)₃([Tris(dibenzylideneacetone)dipalladium(0)]; 0.02 equivalents), S-Phos([2-Dicyclohexylphoshino-2′,6′-dimethoxy-1,1′-biphenyl]; 0.08equivalents) and tribasic potassium phosphate (3.00 equivalents) arestirred under nitrogen atmosphere in a toluene/water mixture (ratio of4:1) at 110° C. for 15 h. To the reaction mixture Celite® and activecarbon are added and stirred at 110° C. for 15 min.

Subsequently the reaction mixture is hot filtered and the residue washedwith toluene. The reaction mixture is poured into 300 mL of a saturatedsodium chloride solution and extracted with ethyl acetate. The combinedorganic phases are washed with saturated sodium chloride solution, driedover MgSO₄ and the solvent is evaporated under reduced pressure.

The residue is purified by chromatography (or by recrystallization oralternatively is stirred in hot ethanol and filtered) and I1-0 isobtained as solid.

In a subsequent reaction, I1-0 (1.00 equivalents), I0 (1.30equivalents), Pd₂(dba)₃ ([Tris(dibenzylideneacetone)dipalladium(0)];0.04 equivalents), X-Phos(2-(dicyclohexylphosphino)-2″,4″,6″-triisopropylbiphenyl, 0.16equivalents) and tribasic potassium phosphate (2.50 equivalents) arestirred under nitrogen atmosphere in a toluene/water mixture (ratio of4:1) at 110° C. for 15 h. To the reaction mixture Celite® and activecarbon are added and stirred at 110° C. for 15 min.

Subsequently the reaction mixture is hot filtered and the residue washedwith toluene. The reaction mixture is poured into 300 mL of a saturatedsodium chloride solution and extracted with ethyl acetate. The combinedorganic phases are washed with saturated sodium chloride solution, driedover MgSO₄ and the solvent is evaporated under reduced pressure.

The residue is purified by chromatography (or by recrystallization oralternatively is stirred in hot ethanol and filtered) and Z1 is obtainedas solid.

General Procedure for Synthesis AAV2

The synthesis of Z2 is carried out according to AAV1, wherein4-bromo-3-fluorobenzonitrile reacts with 4-chloro-2-fluorophenylboronicester.

4-bromo-3-fluorobenzonitrile (1.00 equivalents),4-chloro-2-fluorophenylboronic ester (1.2 equivalents), Pd₂(dba)₃([Tris(dibenzylideneacetone)dipalladium(0)]; 0.02 equivalents), S-Phos([2-Dicyclohexylphoshino-2′,6′-dimethoxy-1,1′-biphenyl]; 0.08equivalents) and tribasic potassium phosphate (3.00 equivalents) arestirred under nitrogen atmosphere in a toluene/water mixture (ratio of4:1) at 110° C. for 15 h. To the reaction mixture Celite® and activecarbon are added and stirred at 110° C. for 15 min.

Subsequently the reaction mixture is hot filtered and the residue washedwith toluene. The reaction mixture is poured into 300 mL of a saturatedsodium chloride solution and extracted with ethyl acetate. The combinedorganic phases are washed with saturated sodium chloride solution, driedover MgSO₄ and the solvent is evaporated under reduced pressure.

The residue is purified by chromatography (or by recrystallization oralternatively is stirred in hot ethanol and filtered) and I2-0 isobtained as solid.

In a subsequent reaction, I2-0 (1.00 equivalents), I0 (1.30equivalents), Pd₂(dba)₃ ([Tris(dibenzylideneacetone)dipalladium(0)];0.04 equivalents), X-Phos(2-(dicyclohexylphosphino)-2″,4″,6″-triisopropylbiphenyl, 0.16equivalents) and tribasic potassium phosphate (2.50 equivalents) arestirred under nitrogen atmosphere in a toluene/water mixture (ratio of4:1) at 110° C. for 15 h. To the reaction mixture Celite® (kieselgur)and active carbon are added and stirred at 110° C. for 15 min.

Subsequently, the reaction mixture is hot filtered and the residuewashed with toluene. The reaction mixture is poured into 300 mL of asaturated sodium chloride solution and extracted with ethyl acetate. Thecombined organic phases are washed with saturated sodium chloridesolution, dried over MgSO₄ and the solvent is evaporated under reducedpressure.

The residue is purified by chromatography (or by recrystallization oralternatively is stirred in hot ethanol and filtered) and Z2 is obtainedas solid.

General Procedure for Synthesis AAV3

The synthesis of Z3 is carried out according to AAV1, wherein4-bromo-3-fluorobenzonitrile reacts with 5-chloro-2-fluorophenylboronicester.

4-bromo-3-fluorobenzonitrile (1.00 equivalents),5-chloro-2-fluorophenylboronic ester (1.2 equivalents), Pd₂(dba)₃([Tris(dibenzylideneacetone)dipalladium(0)]; 0.02 equivalents), S-Phos([2-Dicyclohexylphoshino-2′,6′-dimethoxy-1,1′-biphenyl]; 0.08equivalents) and tribasic potassium phosphate (3.00 equivalents) arestirred under nitrogen atmosphere in a toluene/water mixture (ratio of4:1) at 110° C. for 15 h. To the reaction mixture Celite® and activecarbon are added and stirred at 110° C. for 15 min.

Subsequently the reaction mixture is hot filtered and the residue washedwith toluene. The reaction mixture is poured into 300 mL of a saturatedsodium chloride solution and extracted with ethyl acetate. The combinedorganic phases are washed with saturated sodium chloride solution, driedover MgSO₄ and the solvent is evaporated under reduced pressure.

The residue is purified by chromatography (or by recrystallization oralternatively is stirred in hot ethanol and filtered) and I3-0 isobtained as solid.

In a subsequent reaction, I3-0 (1.00 equivalents), I0 (1.30equivalents), Pd₂(dba)₃ ([Tris(dibenzylideneacetone)dipalladium(0)];0.04 equivalents), X-Phos(2-(dicyclohexylphosphino)-2″,4″,6″-triisopropylbiphenyl, 0.16equivalents) and tribasic potassium phosphate (2.50 equivalents) arestirred under nitrogen atmosphere in a toluene/water mixture (ratio of4:1) at 110° C. for 15 h. To the reaction mixture Celite® and activecarbon are added and stirred at 110° C. for 15 min.

Subsequently the reaction mixture is hot filtered and the residue washedwith toluene. The reaction mixture is poured into 300 mL of a saturatedsodium chloride solution and extracted with ethyl acetate. The combinedorganic phases are washed with saturated sodium chloride solution, driedover MgSO₄ and the solvent is evaporated under reduced pressure.

The residue is purified by chromatography (or by recrystallization oralternatively is stirred in hot ethanol and filtered) and Z3 is obtainedas solid.

General Procedure for Synthesis AAV4

The synthesis of Z4 is carried out according to AAV1, wherein3-bromo-4-fluorobenzonitrile reacts with 5-chloro-2-fluorophenylboronicester.

3-bromo-4-fluorobenzonitrile (1.00 equivalents),5-chloro-2-fluorophenylboronic ester (1.2 equivalents), Pd₂(dba)₃([Tris(dibenzylideneacetone)dipalladium(0)]; 0.02 equivalents), S-Phos([2-Dicyclohexylphoshino-2′,6′-dimethoxy-1,1′-biphenyl]; 0.08equivalents) and tribasic potassium phosphate (3.00 equivalents) arestirred under nitrogen atmosphere in a toluene/water mixture (ratio of4:1) at 110° C. for 15 h. To the reaction mixture Celite® and activecarbon are added and stirred at 110° C. for 15 min.

Subsequently the reaction mixture is hot filtered and the residue washedwith toluene. The reaction mixture is poured into 300 mL of a saturatedsodium chloride solution and extracted with ethyl acetate. The combinedorganic phases are washed with saturated sodium chloride solution, driedover MgSO₄ and the solvent is evaporated under reduced pressure.

The residue is purified by chromatography (or by recrystallization oralternatively is stirred in hot ethanol and filtered) and I4-0 isobtained as solid.

In a subsequent reaction, I4-0 (1.00 equivalents), I0 (1.30equivalents), Pd₂(dba)₃ ([Tris(dibenzylideneacetone)dipalladium(0)];0.04 equivalents), X-Phos(2-(dicyclohexylphosphino)-2″,4″,6″-triisopropylbiphenyl, 0.16equivalents) and tribasic potassium phosphate (2.50 equivalents) arestirred under nitrogen atmosphere in a toluene/water mixture (ratio of4:1) at 110° C. for 15 h. To the reaction mixture Celite® and activecarbon are added and stirred at 110° C. for 15 min.

Subsequently the reaction mixture is hot filtered and the residue washedwith toluene. The reaction mixture is poured into 300 mL of a saturatedsodium chloride solution and extracted with ethyl acetate. The combinedorganic phases are washed with saturated sodium chloride solution, driedover MgSO₄ and the solvent is evaporated under reduced pressure.

The residue is purified by chromatography (or by recrystallization oralternatively is stirred in hot ethanol and filtered) and Z4 is obtainedas solid.

General Procedure for Synthesis AAV5

Z1, Z2, Z3 or Z4 (1 equivalent each), the corresponding donor moleculeD-H (2.20 equivalents) and tribasic potassium phosphate (4.40equivalents) are suspended under nitrogen atmosphere in DMSO and stirredat 120° C. (20 h). Subsequently the reaction mixture is poured into asaturated sodium chloride solution and the precipitate is filtered andwashed with water. The solid is then dissolved in dichloromethane, driedover MgSO₄ and the solvent is evaporated under reduced pressure. Thecrude product is purified by recrystallization or by flashchromatography. The product is obtained as a solid.

In particular, the donor molecule D-H is a 3,6-substituted carbazole(e.g., 3,6-dimethylcarbazole, 3,6-diphenylcarbazole,3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g.,2,7-dimethylcarbazole, 2,7-diphenylcarbazole,2,7-di-tert-butylcarbazole), a 1,8-substituted carbazole (e.g.,1,8-dimethylcarbazole, 1,8-diphenylcarbazole,1,8-di-tert-butylcarbazole), a 1-substituted carbazole (e.g.,1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), a2-substituted carbazole (e.g., 2-methylcarbazole, 2-phenylcarbazole,2-tert-butylcarbazole), or a 3-substituted carbazole (e.g.,3-methylcarbazole, 3-phenylcarbazole, 3-tert-butylcarbazole).

For example, a halogen-substituted carbazole, particularly3-bromocarbazole, can be used as D-H.

In a subsequent reaction a boronic acid ester functional group orboronic acid functional group may be exemplarily introduced at theposition of the one or more halogen substituents, which was introducedvia D-H, to yield the corresponding carbazol-3-ylboronic acid ester orcarbazol-3-ylboronic acid, e.g., via the reaction withbis(pinacolato)diboron (CAS No. 73183-34-3). Subsequently, one or moresubstituents R^(a) may be introduced in place of the boronic acid estergroup or the boronic acid group via a coupling reaction with thecorresponding halogenated reactant R^(a)-Hal, preferably R^(a)—Cl andR^(a)—Br.

Alternatively, one or more substituents R^(a) may be introduced at theposition of the one or more halogen substituents, which was introducedvia D-H, via the reaction with a boronic acid of the substituent R^(a)[R^(a)—B(OH)₂] or a corresponding boronic acid ester.

Cyclic Voltammetry

Cyclic voltammograms are measured from solutions having concentration of10⁻³ mol/L of the organic molecules in dichloromethane or a suitablesolvent and a suitable supporting electrolyte (e.g. 0.1 mol/L oftetrabutylammonium hexafluorophosphate). The measurements are conductedat room temperature under nitrogen atmosphere with a three-electrodeassembly (Working and counter electrodes: Pt wire, reference electrode:Pt wire) and calibrated using FeCp₂/FeCp₂ ⁺ as internal standard. TheHOMO data was corrected using ferrocene as internal standard againstSCE.

Density Functional Theory Calculation

Molecular structures are optimized employing the BP86 functional and theresolution of identity approach (RI). Excitation energies are calculatedusing the (BP86) optimized structures employing Time-Dependent DFT(TD-DFT) methods. Orbital and excited state energies are calculated withthe B3LYP functional. Def2-SVP basis sets (and a m4-grid for numericalintegration are used. The Turbomole program package is used for allcalculations.

Photophysical Measurements

Sample pretreatment: Spin-coating

Apparatus: Spin150, SPS euro.

The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

Program: 1) 3 s at 400 U/min; 20 s at 1000 U/min at 1000 Upm/s. 3) 10 sat 4000 U/min at 1000 Upm/s. After coating, the films are tried at 70°C. for 1 min.

Photoluminescence Spectroscopy and TCSPC (Time-Correlated Single-PhotonCounting)

Steady-state emission spectroscopy is measured by a Horiba Scientific,Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- andemissions monochromators and a Hamamatsu R928 photomultiplier and atime-correlated single-photon counting option.

Emissions and excitation spectra are corrected using standard correctionfits.

Excited state lifetimes are determined employing the same system usingthe TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

Excitation Sources:

NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)

NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

SpectraLED 310 (wavelength: 314 nm)

SpectraLED 355 (wavelength: 355 nm).

Data analysis (exponential fit) is done using the software suiteDataStation and DAS6 analysis software. The fit is specified using thechi-squared-test.

Photoluminescence Quantum Yield Measurements

For photoluminescence quantum yield (PLQY) measurements an Absolute PLQuantum Yield Measurement C9920-03G system (Hamamatsu Photonics) isused. Quantum yields and CIE coordinates are determined using thesoftware U6039-05 version 3.6.0.

Emission maxima are given in nm, quantum yields ϕ in % and CIEcoordinates as x,y values. PLQY is determined using the followingprotocol:

-   -   1) Quality assurance: Anthracene in ethanol (known        concentration) is used as reference    -   2) Excitation wavelength: the absorption maximum of the organic        molecule is determined and the molecule is excited using this        wavelength    -   3) Measurement        -   Quantum yields are measured, for sample, of solutions or            films under nitrogen atmosphere. The yield is calculated            using the equation:

$\Phi_{PL} = {\frac{n_{photon},{emited}}{n_{photon},{absorbed}} = \frac{\int{{\frac{\lambda}{hc}\left\lbrack {{{Int}_{emitted}^{sample}(\lambda)} - {{Int}_{absorbed}^{sample}(\lambda)}} \right\rbrack}d\; \lambda}}{\int{{\frac{\lambda}{hc}\left\lbrack {{{Int}_{emitted}^{reference}(\lambda)} - {{Int}_{absorbed}^{reference}(\lambda)}} \right\rbrack}d\; \lambda}}}$

-   -   wherein n_(photon) denotes the photon count and Int. the        intensity.

Production and Characterization of Optoelectronic Devices

OLED devices comprising organic molecules according to the invention canbe produced via vacuum-deposition methods. If a layer contains more thanone compound, the weight-percentage of one or more compounds is given in%. The total weight-percentage values amount to 100%, thus if a value isnot given, the fraction of this compound equals to the differencebetween the given values and 100%.

The not fully optimized OLEDs are characterized using standard methodsand measuring electroluminescence spectra, the external quantumefficiency (in %) in dependency on the intensity, calculated using thelight detected by the photodiode, and the current. The OLED devicelifetime is extracted from the change of the luminance during operationat constant current density. The LT50 value corresponds to the time,where the measured luminance decreased to 50% of the initial luminance,analogously LT80 corresponds to the time point, at which the measuredluminance decreased to 80% of the initial luminance, LT 95 to the timepoint, at which the measured luminance decreased to 95% of the initialluminance etc. Accelerated lifetime measurements are performed (e.g.applying increased current densities). Exemplarily LT80 values at 500cd/m² are determined using the following equation:

${{LT}\; 80\mspace{14mu} \left( {500\frac{{cd}^{2}}{m^{2}}} \right)} = {{LT}\; 80\left( L_{0} \right)\mspace{14mu} \left( \frac{L_{0}}{500\frac{{cd}^{2}}{m^{2}}} \right)^{1.6}}$

wherein L₀ denotes the initial luminance at the applied current density.

The values correspond to the average of several pixels (typically two toeight), the standard deviation between these pixels is given.

HPLC-MS:

HPLC-MS spectroscopy is performed on a HPLC by Agilent (1100 series)with MS-detector (Thermo LTQ XL). A reverse phase column 4.6 mm×150 mm,particle size 5.0 μm from Waters (without pre-column) is used in theHPLC. The HPLC-MS measurements are performed at room temperature (rt)with the solvents acetonitrile, water and THF in the followingconcentrations:

-   solvent A: H₂O (90%) MeCN (10%)-   solvent B: H₂O (10%) MeCN (90%) THF-   solvent C: (100%)

From a solution with a concentration of 0.5 mg/ml an injection volume of15 μL is taken for the measurements. The following gradient is used:

Flow rate time A B D [ml/min] [min] [%] [%] [%] 3 0 40 50 10 3 10 10 1575 3 16 10 15 75 3 16.01 40 50 10 3 20 40 50 10

Ionisation of the probe is performed by APCI (atmospheric pressurechemical ionization).

Example 1

Example 1 was synthesized according to AAV3 and AAV5, wherein thesynthesis AAV5 had a yield of 14%.

FIG. 1 depicts the emission spectrum of example 1 (10% by weight inPMMA). The emission maximum (λ_(max)) is at 465 nm. Thephotoluminescence quantum yield (PLQY) is 77%, the full width at halfmaximum (FWHM) is 0.39 eV and the emission lifetime is 82 μs. Theresulting CIE_(x) coordinate is determined at 0.15 and the CIE_(y)coordinate at 0.18.

Example 2

Example 2 was synthesized according to AAV3 and AAV5, wherein thesynthesis AAV5 had a yield of 28%.

MS (HPLC-MS):

Molecular Retention m/z m/z Formula Time calculated found C₆₉H₄₁F₆N₃14.31 min 1025.32 1025.35

FIG. 2 depicts the emission spectrum of example 2 (10% by weight inPMMA). The emission maximum (λ_(max)) is at 464 nm. Thephotoluminescence quantum yield (PLQY) is 71%, the full width at halfmaximum (FWHM) is 0.39 eV and the emission lifetime is 99 μs. Theresulting CIE_(x) coordinate is determined at 0.15 and the CIE_(y)coordinate at 0.18.

Example 3

Example 3 was synthesized according to AAV3 and AAV5, wherein thesynthesis AAV5 had a yield of 29%.

MS (HPLC-MS):

Molecular Retention m/z m/z Formula Time calculated found C₅₇H₃₃F₆N₃12.05 min 873.26 873.35

FIG. 3 depicts the emission spectrum of example 3 (10% by weight inPMMA). The emission maximum (λ_(max)) is at 461 nm. Thephotoluminescence quantum yield (PLQY) is 69%, the full width at halfmaximum (FWHM) is 0.40 eV and the emission lifetime is 136 μs. Theresulting CIE_(X) coordinate is determined at 0.15 and the CIE_(y)coordinate at 0.16.

ADDITIONAL EXAMPLES OF THE INVENTION

Although illustrative embodiments of the present invention have beendescribed herein with reference to the accompanying drawings, it is tobe understood that the invention is not limited to those preciseembodiments, and that various other changes and modifications may bemade by one skilled in the art without departing from the scope orspirit of the invention.

What is claimed is:
 1. An organic molecule, comprising one firstchemical moiety comprising a structure of formula I,

and two second chemical moieties, each independently from anothercomprising a structure of formula II,

wherein the first chemical moiety is linked to each of the two secondchemical moieties via a single bond; wherein T is selected from thegroup consisting of the binding site of a single bond linking the firstchemical moiety to one of the two second chemical moieties, R^(A) andR¹; V is selected from the group consisting of the binding site of asingle bond linking the first chemical moiety to one of the two secondchemical moieties, R^(A) and R¹; W is selected from the group consistingof the binding site of a single bond linking the first chemical moietyto one of the two second chemical moieties, R^(A) and R¹; X is selectedfrom the group consisting of the binding site of a single bond linkingthe first chemical moiety to one of the two second chemical moieties,R^(A) and R¹; Y is selected from the group consisting of the bindingsite of a single bond linking the first chemical moiety to one of thetwo second chemical moieties, R^(A) and R¹; R^(A) is consisting of astructure of formula A1,

wherein $ represents the binding site of the single bond connectingR^(A) to the first chemical moiety as shown in formula I; A^(I), A^(II),A^(III), A^(IV) and A^(V) are each selected from the group consisting ofCF₃ and R^(I); R^(T) is selected from the group consisting of thebinding site of a single bond linking the first chemical moiety to oneof the two second chemical moieties, CN and R²; R^(V) is selected fromthe group consisting of the binding site of a single bond linking thefirst chemical moiety to one of the two second chemical moieties, CN andR²; R^(W) is selected from the group consisting of the binding site of asingle bond linking the first chemical moiety to one of the two secondchemical moieties, CN and R²; R^(X) is selected from the groupconsisting of the binding site of a single bond linking the firstchemical moiety to one of the two second chemical moieties, CN and R²;R^(Y) is selected from the group consisting of the binding site of asingle bond linking the first chemical moiety to one of the two secondchemical moieties, CN and R²; # represents the binding site of a singlebond linking the second chemical moieties to the first chemical moiety;Z is at each occurrence independently from another selected from thegroup consisting of a direct bond, CR³R⁴, C═CR³R⁴, C═O, C═NR³, NR³, O,SiR³R⁴, S, S(O) and S(O)₂; R¹ is at each occurrence independently fromanother selected from the group consisting of: hydrogen, deuterium,C₁-C₅-alkyl, wherein one or more hydrogen atoms are optionallysubstituted by deuterium; C₂-C₈-alkenyl, wherein one or more hydrogenatoms are optionally substituted by deuterium; C₂-C₈-alkynyl, whereinone or more hydrogen atoms are optionally substituted by deuterium; andC₆-C₁₈-aryl, which is optionally substituted with one or moresubstituents selected from the group consisting of hydrogen, deuterium,OPh, C₁-C₅-alkyl, C₂-C₅-alkenyl and C₂-C₅-alkynyl. R² is at eachoccurrence independently from another selected from the group consistingof: hydrogen, deuterium, C₁-C₅-alkyl, wherein one or more hydrogen atomsare optionally substituted by deuterium; C₂-C₈-alkenyl, wherein one ormore hydrogen atoms are optionally substituted by deuterium;C₂-C₈-alkynyl, wherein one or more hydrogen atoms are optionallysubstituted by deuterium; and C₆-C₁₈-aryl, which is optionallysubstituted with one or more substituents selected from the groupconsisting of hydrogen, deuterium, OPh, C₁-C₅-alkyl, C₂-C₅-alkenyl andC₂-C₅-alkynyl. R^(I) is at each occurrence independently from anotherselected from the group consisting of hydrogen, deuterium, C₁-C₅-alkyl,wherein one or more hydrogen atoms are optionally substituted bydeuterium; and C₆-C₁₈-aryl, which is optionally substituted with one ormore substituents R⁶. R^(a), R³ and R⁴ is at each occurrenceindependently from another selected from the group consisting of:hydrogen, deuterium, N(R⁵)₂, OR⁵, Si(R⁵)₃, B(OR⁵)₂, OSO₂R⁵, CF₃, CN, F,Br, I, C₁-C₄₀-alkyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₁-C₄₀-alkoxy,which is optionally substituted with one or more substituents R⁵ andwherein one or more non-adjacent CH₂-groups are optionally substitutedby R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵,P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₁-C₄₀-thioalkoxy, which isoptionally substituted with one or more substituents R⁵ and wherein oneor more non-adjacent CH₂-groups are optionally substituted by R⁵C═CR⁵,C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO,SO₂, NR⁵, O, S or CONR⁵; C₂-C₄₀-alkenyl, which is optionally substitutedwith one or more substituents R⁵ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂,Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁵; andC₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁵; R⁵ is at each occurrence independently from anotherselected from the group consisting of hydrogen, deuterium, N(R⁶)₂, OR⁶,Si(R⁶)₃, B(OR⁶)₂, OSO₂R⁶, CF₃, CN, F, Br, I, C₁-C₄₀-alkyl, which isoptionally substituted with one or more substituents R⁶ and wherein oneor more non-adjacent CH₂-groups are optionally substituted by R⁶C═CR⁶,C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O, C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO,SO₂, NR⁶, O, S or CONR⁶; C₁-C₄₀-alkoxy, which is optionally substitutedwith one or more substituents R⁶ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂,Sn(R⁶)₂, C═O, C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;C₁-C₄₀-thioalkoxy, which is optionally substituted with one or moresubstituents R⁶ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;C₂-C₄₀-alkenyl, which is optionally substituted with one or moresubstituents R⁶ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁶ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁶; andC₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁶; R⁶ is at each occurrence independently from anotherselected from the group consisting of: hydrogen, deuterium, OPh, CF₃,CN, F, C₁-C₅-alkyl, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₁-C₅-alkoxy, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₁-C₅-thioalkoxy, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₂-C₅-alkenyl, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₂-C₅-alkynyl, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₆-C₁₈-aryl, which is optionally substituted with one or moreC₁-C₅-alkyl substituents; C₃-C₁₇-heteroaryl, which is optionallysubstituted with one or more C₁-C₅-alkyl substituents; N(C₆-C₁₈-aryl)₂,N(C₃-C₁₇-heteroaryl)₂, and N(C₃-C₁₇-heteroaryl)(C₆-C₁₈-aryl); whereinthe substituents R^(a), R³, R⁴ or R⁵ optionally form, independently fromeach other, a mono- or polycyclic, aliphatic, aromatic and/orbenzo-fused ring system with one or more substituents R^(a), R³, R⁴ orR⁵; wherein exactly one substituent selected from the group consistingof T, V, W, X and Y is R^(A); exactly one substituent selected from thegroup consisting of R^(T), R^(V), R^(W), R^(X) and R^(Y) is CN; exactlyone substituent selected from the group consisting of T, V, W, X and Yrepresents the binding site of a single bond linking the first chemicalmoiety to one of the two second chemical moieties; exactly onesubstituent selected from the group consisting of R^(T), R^(V), R^(W),R^(X) and R^(Y) represents the binding site of a single bond linking thefirst chemical moiety to one of the two second chemical moieties; andexactly two substituents selected from the group consisting of A^(I),A^(II), A^(III), A^(IV) and A^(V) are CF₃.
 2. The organic moleculeaccording to claim 1, wherein exactly one substituent selected from thegroup consisting of T, V and W is R^(A); exactly one substituentselected from the group consisting of R^(T), R^(V) and R^(W) is CN;exactly one substituent selected from the group consisting of W, Y and Xrepresents the binding site of a single bond linking the first chemicalmoiety to one of the two second chemical moieties; exactly onesubstituent selected from the group consisting of R^(W), R^(X) and R^(Y)represents the binding site of a single bond linking the first chemicalmoiety to one of the two second chemical moieties.
 3. The organicmolecule according to claim 1, wherein the first chemical moietycomprises a structure of formula Ia:

wherein Y^(D) represents the binding site of a single bond linking thefirst chemical moiety and one of the two second chemical moieties;R^(YD) represents the binding site of a single bond linking the firstchemical moiety and one of the two second chemical moieties; Q isindependently from each other at each occurrence selected from the groupconsisting of R¹ and R^(A); R^(Q) is independently from each other ateach occurrence selected from the group consisting of R² and CN; whereinexactly one substituent R^(Q) is CN; and wherein exactly one substituentQ is R^(A).
 4. The organic molecule according to claim 1, wherein R¹, R²and R^(I) are individually at each occurrence independently from anotherselected from the group consisting of H, methyl, mesityl, tolyl, andphenyl.
 5. The organic molecule according to claim 1, wherein each ofthe two second chemical moieties independently from another comprise astructure of formula IIa:


6. The organic molecule according to claim 5, wherein each of the twosecond chemical moieties independently from another comprise a structureof formula IIb:

wherein R^(b) is at each occurrence independently from another selectedfrom the group consisting of: deuterium, N(R⁵)₂, OR⁵, Si(R⁵)₃, B(OR⁵)₂,OSO₂R⁵, CF₃, CN, F, Br, I, C₁-C₄₀-alkyl, which is optionally substitutedwith one or more substituents R⁵ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂,Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-alkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-thioalkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkenyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁵; andC₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁵; and wherein apart from that the definitions in claim 1apply.
 7. The organic molecule according to claim 5, wherein each of thetwo second chemical moieties independently from another comprise astructure of formula IIc:

wherein R^(b) is at each occurrence independently from another selectedfrom the group consisting of deuterium, N(R⁵)₂, OR⁵, Si(R⁵)₃, B(OR⁵)₂,OSO₂R⁵, CF₃, CN, F, Br, I, C₁-C₄₀-alkyl, which is optionally substitutedwith one or more substituents R⁵ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂,Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-alkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-thioalkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkenyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁵; andC₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁵; and wherein apart from that the definitions in claim 1apply.
 8. The organic molecule according to claim 6, wherein each R^(b)is independently from another selected from the group consisting of: Me,^(i)Pr, ^(t)Bu, CN, CF₃, Ph, which is optionally substituted with one ormore substituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; pyridinyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃ and Ph; pyrimidinyl, which is optionally substituted with one ormore substituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; carbazolyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃ and Ph; triazinyl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph; and N(Ph)₂.
 9. Theorganic molecule according to claim 7, wherein each R^(b) isindependently from another selected from the group consisting of: Me,^(i)Pr, ^(t)Bu, CN, CF₃, Ph, which is optionally substituted with one ormore substituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; pyridinyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃ and Ph; pyrimidinyl, which is optionally substituted with one ormore substituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; carbazolyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃ and Ph; triazinyl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph; and N(Ph)₂.
 10. Acomposition, comprising: (a) at least one organic molecule according toclaim 1, and (b) one or more emitter and/or host materials, which differfrom the organic molecule of claim 1, and (c) optionally, one or moredyes and/or one or more solvents.
 11. The composition according to claim10, wherein the at least one organic molecule according to claim 1 is inthe form of an emitter and/or a host.
 12. An optoelectronic device,comprising an organic molecule according to claim 1 or a compositionaccording to claim
 10. 13. The optoelectronic device according to claim12 in form of a device selected from the group consisting of organiclight-emitting diode (OLED), light-emitting electrochemical cell,OLED-sensor, organic diode, organic solar cell, organic transistor,organic field-effect transistor, organic laser and down-conversionelement.
 14. The optoelectronic device according to claim 12,comprising: a substrate, an anode, and a cathode, wherein the anode orthe cathode are disposed on a substrate, and at least one light-emittinglayer, which is arranged between the anode and the cathode and whichcomprises an organic molecule according to claim 1 or a compositionaccording to claim
 12. 15. The optoelectronic device according to claim12, wherein the organic molecule according to claim 1 is used as aluminescent emitter and/or as a host material and/or as an electrontransport material and/or as a hole injection material and/or as a holeblocking material.
 16. A method for producing an optoelectronic device,wherein an organic molecule according to claim 1 or a compositionaccording to claim 10 is deposited on a solid support.
 17. The methodfor producing an optoelectronic device of claim 16, wherein the organicmolecule is deposited by a vacuum evaporation method or from a solution.